Process of making phenylorthotolylguanidine



.grou o Peleeiegl May 8,

ence STATESPATENT OFFICE,

IRALIEE V. EEUER, 0F PORTSMOUTH, N EW HAMPSHIRE, ASSIGNOR, BY L'IESNE AS- SEGNIJZEHTE, T0 ALBERT C. BURRAGE, OF BOSTON, MASSACKUSETTS.

EBDGESS F O15 MAKING IHENYLORTHOTDLYLGUANIDINE.

Ii'o Brewing.

In the manufacture of rubbei organic accelerceors commonly emplcyed to hasten the Wulcenizing process and amongsuch abeelereizors the various substitutei guani- (lines have found especial favor among rubbei' ,msnu'iacfcurers. I have new discovered acertain group of compounds which possess all the characteristics desirable in a, rubber eccclei'eter and in WhOSGQI'EPQIfiilOH a by product cf the manufacture oi' pei-atoluidine mey eil'ectively be utilized. These new compounds use of especial interest in that they ere guaroicline derivatives having an aryl radical substituted for one hydrogen. atom clone amino gi-oup and e. different aryl radicel in piece ci a hydrogen atom oi? the other amino group.

This compound, having an aryl radical subs stituiecl'iior a hydfogen. atom in one amino and an unlike aryl radical in place of mhydrogen atom in its other amino group may properly be termed phenyltolylthioutee when, as in this specific example, the unlike radicals are phenyl and tolyl, respec Lively. This new compound has a melting point of approximately "132 C. and the 3mm described xeection is nearly iii-icicle e gn Application fleii Bebmary 27, 1923. Serial No. 621,686,

' The substance phenylorthotblylguanidine is cited as a specific instance Of the genus of compounds which I refer to. This'is e definite chemical compound, having ,the formula e- NH It is a white, flufiy, non-hygroscopic powder having a melting point 0f-130.3 U. and does not become gum my on heating.

As a first step in the process of prcucing this substance, aniline (G H 'IIH aml or thotoluidine (C HANH LGH in molecw lar proportions, with an excess of carbon bi sul lphide {(3252} are caused to react with each other, the action proceeding according to the following equation:

CH1: NH OS: 'o-; l is "\m/ thee which should thecifeticeliy be ebteizb able.

The second step of the process may be carried out in various ways In eccocdsmce with one, the finely pulverized phenyltolylihiouree. is heeled f'h alcohcdic ammonia and, litherge at ewe t low tempera lore, and. with vigorous mtimi the reactien taking lolace in eccor ience with film equation 7 3 r amen e we The resulting substituted guanidinemitrate I claim:

salt is afterward converted according to well That method of preparing phenylorthotolknawn methods into phenylorthotdlyl-guaniylguamidine which comprises treating ani- 15 dine base, which is adefinite Chemical C line and orthotoluidine in molecular propor- :3 Pound 6f the formula tions with carbon bisulphide to form phenylom orthotolylthiourea and by d esulphurization C converting the latter into a, substituted guan- E idine. 20

-NH Signed by me at Boston, Massachusetts, 1 firs-( v this 20th day of February 1923.

T 'and'having the properties aforementioned. RALPH v. HIEUSER. 

